Cherilus was the only redshirt freshman to start for the Eagles, lining up at right tackle for all 12 games and delivered six touchdown-resulting blocks and 46 knockdowns, he finished with an 80.1 percent grade for blocking consistency, as he paved the way for 100-yard rushing performances from L. V. Whitworth, Andre Callender and A. J. Brooks. He helped the Eagles to average 385.4 yards per game in total offense.

He started all 12 contests at right tackle during 2005 season, collecting 53 knockdowns with seven touchdown-resulting blocks . He worked well with right guard Josh Beekman, as the pair helped the Eagles lead the Atlantic Coast in total offense with 387.75 yards per game and rank third in passing with 242.75 yards per game. The Eagles offensive line was ranked twelfth in the nation, allowing only 15 sacks for losses totaling 91 yards.

In 2006, Cherilus started in all 13 games at right tackle and paved the way for seven 100-yard rushing games and a collective 1,424 rushing yards by L. V. Whitworth and Andre Callender. He helped the team average 114.5 yards per game on the ground and 355.6 yards in total offense, as the front wall allowed only 22 sacks for the season. He was graded 78.77 percent for blocking consistency while collecting 79 knockdowns along with 10 touchdown-resulting blocks. He played at the 2006 Meineke Car Care Bowl win over Navy.

He was named all-ACC second-team selection and recipient of the team’s Unsung Hero Award, Cherilus started 14 games at left tackle, helping BC rank seventh in the nation with an average of 323.9 yards per game passing, he registered 77 knockdowns with twelve touchdown-resulting blocks, finishing with a 78.0 percent grade for blocking consistency and also helped hold opponents to only 61 tackles-for-loss (fifth in the nation) and 22 sacks.

He received probation along with DeJuan Tribble for assault with a deadly weapon for his role in an attack on a patron at The Greatest Bar in Boston. He was also accompanied by Jo-Lonn Dunbar and Joseph Boike during this assault.

On March 12, 2013, Cherilus signed with the Indianapolis Colts.[2] He plays the RT position opposite LT Anthony Castonzo. In 2013, he started all 16 games and started in the Colts' 2 postseason games. In 2014, Cherilus started 13 games, including his 100th career start in week 15. He missed the final two weeks of the regular season due to injury, and was placed on season-ending injured reserve on December 31.[3]